2. Academic Validation
  3. Derivatization of the C12-C13 functional groups of epothilones A, B and C

Derivatization of the C12-C13 functional groups of epothilones A, B and C

  • Bioorg Med Chem Lett. 1998 Nov 3;8(21):3031-6. doi: 10.1016/S0960-894X(98)00546-0.
M Sefkow 1,  M Kiffe,  G Höfle
Affiliations

Affiliation

  • 1 Gesellschaft für Biotechnologische Forschung mbH, Abt. Naturstoffchemie, Germany. [email protected]
PMID: 9873670 DOI: 10.1016/S0960-894X(98)00546-0
Abstract

Epothilone A reacted with hydrohalic acids to C12-C13 halohydrin regioisomers (ratios: 2:1-4:1), whereas epothilone B gave under the same conditions the isomerically pure C12 halo C13 hydroxy derivative. With non-nucleophilic Brønstedt acids and with Lewis acids a highly solvent dependent product distribution and some unexpected rearrangement products were observed. Epothilone C bearing a double bond between C12 and C13 was regioselectively dihydroxylated or hydrogenated at that position.

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